RU2009118488A - IMIDAZOLONE AND IMIDAZOLIDINONE DERIVATIVES AS 11B-HSD1 DIABETES INHIBITORS - Google Patents
IMIDAZOLONE AND IMIDAZOLIDINONE DERIVATIVES AS 11B-HSD1 DIABETES INHIBITORS Download PDFInfo
- Publication number
- RU2009118488A RU2009118488A RU2009118488/04A RU2009118488A RU2009118488A RU 2009118488 A RU2009118488 A RU 2009118488A RU 2009118488/04 A RU2009118488/04 A RU 2009118488/04A RU 2009118488 A RU2009118488 A RU 2009118488A RU 2009118488 A RU2009118488 A RU 2009118488A
- Authority
- RU
- Russia
- Prior art keywords
- hydroxyadamantan
- methyl
- adamantan
- imidazolidin
- methylimidazolidin
- Prior art date
Links
- 206010012601 diabetes mellitus Diseases 0.000 title claims 3
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 title 1
- 150000008624 imidazolidinones Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- -1 hydroxyadamantyl Chemical group 0.000 claims abstract 43
- 150000001875 compounds Chemical class 0.000 claims abstract 30
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 17
- 239000001257 hydrogen Substances 0.000 claims abstract 17
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 11
- 150000002431 hydrogen Chemical group 0.000 claims abstract 11
- 125000001424 substituent group Chemical group 0.000 claims abstract 11
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract 6
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims abstract 6
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 6
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical group C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 3
- 150000001924 cycloalkanes Chemical class 0.000 claims abstract 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 3
- 125000003566 oxetanyl group Chemical group 0.000 claims abstract 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract 3
- BFDGXHHCTLJIHH-UHFFFAOYSA-N 5-phenyl-3-[3-(trifluoromethyl)phenyl]-1h-imidazol-2-one Chemical compound FC(F)(F)C1=CC=CC(N2C(NC(=C2)C=2C=CC=CC=2)=O)=C1 BFDGXHHCTLJIHH-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 150000002148 esters Chemical class 0.000 claims abstract 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract 2
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract 2
- 150000001408 amides Chemical class 0.000 claims 26
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 24
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 8
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 claims 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 6
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims 5
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 claims 5
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 5
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 4
- 239000004202 carbamide Substances 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- XXLXDTGJEATQOW-CGAUPDFVSA-N (4r)-1-(2-adamantyl)-3-methyl-4-propan-2-ylimidazolidin-2-one Chemical compound O=C1N(C)[C@H](C(C)C)CN1C1C(C2)CC3CC2CC1C3 XXLXDTGJEATQOW-CGAUPDFVSA-N 0.000 claims 2
- GDOBAHJVBZQCFD-DUTNFGBUSA-N (4s)-1-(2-adamantyl)-4-propan-2-ylimidazolidin-2-one Chemical compound O=C1N[C@@H](C(C)C)CN1C1C(C2)CC3CC2CC1C3 GDOBAHJVBZQCFD-DUTNFGBUSA-N 0.000 claims 2
- GNPWKNZBWAYWQU-UHFFFAOYSA-N 1-(2-adamantyl)-3,4-dicyclopropyl-4-methylimidazolidin-2-one Chemical compound C1CC1C1(C)CN(C2C3CC4CC(C3)CC2C4)C(=O)N1C1CC1 GNPWKNZBWAYWQU-UHFFFAOYSA-N 0.000 claims 2
- VFYHLPKDHHKRGZ-UHFFFAOYSA-N 1-(2-adamantyl)-3,4-dicyclopropylimidazolidin-2-one Chemical compound C1CC1N1C(=O)N(C2C3CC4CC(C3)CC2C4)CC1C1CC1 VFYHLPKDHHKRGZ-UHFFFAOYSA-N 0.000 claims 2
- KMLLNFXKVOMAKB-UHFFFAOYSA-N 1-(2-adamantyl)-4,4-dimethylimidazolidin-2-one Chemical compound O=C1NC(C)(C)CN1C1C(C2)CC3CC2CC1C3 KMLLNFXKVOMAKB-UHFFFAOYSA-N 0.000 claims 2
- XCHXGNOMKHBNEC-UHFFFAOYSA-N 1-(2-adamantyl)-4-(cyclopropylmethyl)imidazolidin-2-one Chemical compound C1N(C2C3CC4CC(C3)CC2C4)C(=O)NC1CC1CC1 XCHXGNOMKHBNEC-UHFFFAOYSA-N 0.000 claims 2
- FKZAALGDPREXSO-UHFFFAOYSA-N 1-(2-adamantyl)-4-cyclopropyl-4-methylimidazolidin-2-one Chemical compound C1N(C2C3CC4CC(C3)CC2C4)C(=O)NC1(C)C1CC1 FKZAALGDPREXSO-UHFFFAOYSA-N 0.000 claims 2
- OSIYVNPKQGYLEU-UHFFFAOYSA-N 1-(2-adamantyl)-4-methyl-4-propan-2-ylimidazolidin-2-one Chemical compound O=C1NC(C(C)C)(C)CN1C1C(C2)CC3CC2CC1C3 OSIYVNPKQGYLEU-UHFFFAOYSA-N 0.000 claims 2
- KKHCSTBRAUHVCU-UHFFFAOYSA-N 1-cyclopropyl-3-(4-hydroxyphenyl)-1,3-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(O)=CC=C1N1C(=O)N(C2CC2)C2(CCCCC2)C1 KKHCSTBRAUHVCU-UHFFFAOYSA-N 0.000 claims 2
- NEBWCYDOSALZNS-UHFFFAOYSA-N 1-cyclopropyl-3-(4-methoxyphenyl)-1,3-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)N(C2CC2)C2(CCCCC2)C1 NEBWCYDOSALZNS-UHFFFAOYSA-N 0.000 claims 2
- NVNCHWVQPMFLQW-UHFFFAOYSA-N 1-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound FC(F)(F)C1=CC=CC=C1N1C(=O)N(C2CC2)C2(CCCCC2)C1 NVNCHWVQPMFLQW-UHFFFAOYSA-N 0.000 claims 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
- HEIXQXCVGVJAMB-UHFFFAOYSA-N 3,4-dicyclopropyl-1-[2-(trifluoromethyl)phenyl]imidazolidin-2-one Chemical compound FC(F)(F)C1=CC=CC=C1N1C(=O)N(C2CC2)C(C2CC2)C1 HEIXQXCVGVJAMB-UHFFFAOYSA-N 0.000 claims 2
- WTCAWNKMSHXIGK-UHFFFAOYSA-N 3-(2-adamantyl)-1,3-diazaspiro[4.4]nonan-2-one Chemical compound C1N(C2C3CC4CC(C3)CC2C4)C(=O)NC21CCCC2 WTCAWNKMSHXIGK-UHFFFAOYSA-N 0.000 claims 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 2
- LROVVMGKVUDCNJ-UHFFFAOYSA-N 3-cyclopropyl-1-(2,5-dichlorophenyl)-4-propan-2-ylimidazolidin-2-one Chemical compound CC(C)C1CN(C=2C(=CC=C(Cl)C=2)Cl)C(=O)N1C1CC1 LROVVMGKVUDCNJ-UHFFFAOYSA-N 0.000 claims 2
- HJQNHOXZOSNMFT-UHFFFAOYSA-N 3-cyclopropyl-4-propan-2-yl-1-[2-(trifluoromethyl)phenyl]imidazolidin-2-one Chemical compound CC(C)C1CN(C=2C(=CC=CC=2)C(F)(F)F)C(=O)N1C1CC1 HJQNHOXZOSNMFT-UHFFFAOYSA-N 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- PQUILUZIIZWDAE-UHFFFAOYSA-N 4-(1-cyclopropyl-2-oxo-1,3-diazaspiro[4.6]undecan-3-yl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1N1C(=O)N(C2CC2)C2(CCCCCC2)C1 PQUILUZIIZWDAE-UHFFFAOYSA-N 0.000 claims 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- GDOBAHJVBZQCFD-BPHCLYMKSA-N (4r)-1-(2-adamantyl)-4-propan-2-ylimidazolidin-2-one Chemical compound O=C1N[C@H](C(C)C)CN1C1C(C2)CC3CC2CC1C3 GDOBAHJVBZQCFD-BPHCLYMKSA-N 0.000 claims 1
- XXLXDTGJEATQOW-BAPHQMLMSA-N (4s)-1-(2-adamantyl)-3-methyl-4-propan-2-ylimidazolidin-2-one Chemical compound O=C1N(C)[C@@H](C(C)C)CN1C1C(C2)CC3CC2CC1C3 XXLXDTGJEATQOW-BAPHQMLMSA-N 0.000 claims 1
- CXHUONCCMAXQMF-UHFFFAOYSA-N 1'-(4-hydroxyphenyl)-3'-methylspiro[1,3-dihydroindene-2,4'-imidazolidine]-2'-one Chemical compound C1C2(CC3=CC=CC=C3C2)N(C)C(=O)N1C1=CC=C(O)C=C1 CXHUONCCMAXQMF-UHFFFAOYSA-N 0.000 claims 1
- BUQKJTQOZIYEIN-UHFFFAOYSA-N 1'-(4-methoxyphenyl)-3'-methylspiro[1,3-dihydroindene-2,4'-imidazolidine]-2'-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)N(C)C2(CC3=CC=CC=C3C2)C1 BUQKJTQOZIYEIN-UHFFFAOYSA-N 0.000 claims 1
- QSKCALRCUNVODK-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)-3-[(4-fluorophenyl)methyl]-4-propan-2-ylimidazolidin-2-one Chemical compound CC(C)C1CN(C=2C(=CC=C(Cl)C=2)Cl)C(=O)N1CC1=CC=C(F)C=C1 QSKCALRCUNVODK-UHFFFAOYSA-N 0.000 claims 1
- KWMFRYMYSAJWFA-UHFFFAOYSA-N 1-(2-adamantyl)-3-(2-methylpropyl)-4-propan-2-ylimidazolidin-2-one Chemical compound O=C1N(CC(C)C)C(C(C)C)CN1C1C(C2)CC3CC2CC1C3 KWMFRYMYSAJWFA-UHFFFAOYSA-N 0.000 claims 1
- FFZYAPNNNOHIDJ-UHFFFAOYSA-N 1-(2-adamantyl)-3-(cyclobutylmethyl)-4-propan-2-ylimidazol-2-one Chemical compound CC(C)C1=CN(C2C3CC4CC(C3)CC2C4)C(=O)N1CC1CCC1 FFZYAPNNNOHIDJ-UHFFFAOYSA-N 0.000 claims 1
- LCBHDZHDXNQSKQ-UHFFFAOYSA-N 1-(2-adamantyl)-3-(cyclopropylmethyl)-4-(2,2,2-trifluoroethyl)imidazol-2-one Chemical compound FC(F)(F)CC1=CN(C2C3CC4CC(C3)CC2C4)C(=O)N1CC1CC1 LCBHDZHDXNQSKQ-UHFFFAOYSA-N 0.000 claims 1
- LEHFPIJPMMJSCC-UHFFFAOYSA-N 1-(2-adamantyl)-3-(cyclopropylmethyl)-4-propan-2-ylimidazol-2-one Chemical compound CC(C)C1=CN(C2C3CC4CC(C3)CC2C4)C(=O)N1CC1CC1 LEHFPIJPMMJSCC-UHFFFAOYSA-N 0.000 claims 1
- KFNWKRRMRFUOKS-UHFFFAOYSA-N 1-(2-adamantyl)-3-(cyclopropylmethyl)-4-propan-2-ylimidazolidin-2-one Chemical compound CC(C)C1CN(C2C3CC4CC(C3)CC2C4)C(=O)N1CC1CC1 KFNWKRRMRFUOKS-UHFFFAOYSA-N 0.000 claims 1
- NGRKWPVGSBSIEC-UHFFFAOYSA-N 1-(2-adamantyl)-3-(pyridin-2-ylmethyl)imidazol-2-one Chemical compound C1=CN(C2C3CC4CC(C3)CC2C4)C(=O)N1CC1=CC=CC=N1 NGRKWPVGSBSIEC-UHFFFAOYSA-N 0.000 claims 1
- ZVUQQIWKCXGEMJ-UHFFFAOYSA-N 1-(2-adamantyl)-3-benzylimidazol-2-one Chemical compound C1=CN(C2C3CC4CC(C3)CC2C4)C(=O)N1CC1=CC=CC=C1 ZVUQQIWKCXGEMJ-UHFFFAOYSA-N 0.000 claims 1
- ADYSIKCVYMEBCP-UHFFFAOYSA-N 1-(2-adamantyl)-3-cyclopropyl-4,4-dimethylimidazolidin-2-one Chemical compound CC1(C)CN(C2C3CC4CC(C3)CC2C4)C(=O)N1C1CC1 ADYSIKCVYMEBCP-UHFFFAOYSA-N 0.000 claims 1
- UVTMFNMOCNSNKF-UHFFFAOYSA-N 1-(2-adamantyl)-3-cyclopropyl-4-(2-methylpropyl)imidazol-2-one Chemical compound CC(C)CC1=CN(C2C3CC4CC(C3)CC2C4)C(=O)N1C1CC1 UVTMFNMOCNSNKF-UHFFFAOYSA-N 0.000 claims 1
- RTJAGNAPQAFUFU-UHFFFAOYSA-N 1-(2-adamantyl)-3-cyclopropyl-4-(3-fluorophenyl)imidazol-2-one Chemical compound FC1=CC=CC(C=2N(C(=O)N(C3C4CC5CC(C4)CC3C5)C=2)C2CC2)=C1 RTJAGNAPQAFUFU-UHFFFAOYSA-N 0.000 claims 1
- DQABXEOZSSFJQP-UHFFFAOYSA-N 1-(2-adamantyl)-3-cyclopropyl-4-phenylimidazol-2-one Chemical compound C1CC1N1C(=O)N(C2C3CC4CC(C3)CC2C4)C=C1C1=CC=CC=C1 DQABXEOZSSFJQP-UHFFFAOYSA-N 0.000 claims 1
- QXZSWUFTYHYCIJ-UHFFFAOYSA-N 1-(2-adamantyl)-3-cyclopropyl-4-propan-2-ylimidazol-2-one Chemical compound CC(C)C1=CN(C2C3CC4CC(C3)CC2C4)C(=O)N1C1CC1 QXZSWUFTYHYCIJ-UHFFFAOYSA-N 0.000 claims 1
- ZGGOBGZOUXYZGR-UHFFFAOYSA-N 1-(2-adamantyl)-3-cyclopropyl-4-pyridin-2-ylimidazol-2-one Chemical compound C1CC1N1C(=O)N(C2C3CC4CC(C3)CC2C4)C=C1C1=CC=CC=N1 ZGGOBGZOUXYZGR-UHFFFAOYSA-N 0.000 claims 1
- ZUQXQABJIDKAAL-UHFFFAOYSA-N 1-(2-adamantyl)-3-methyl-4-(2,2,2-trifluoroethyl)imidazol-2-one Chemical compound O=C1N(C)C(CC(F)(F)F)=CN1C1C(C2)CC3CC2CC1C3 ZUQXQABJIDKAAL-UHFFFAOYSA-N 0.000 claims 1
- SBXXSLRWSLQYLF-UHFFFAOYSA-N 1-(2-adamantyl)-4-(2-methylpropyl)imidazolidin-2-one Chemical compound O=C1NC(CC(C)C)CN1C1C(C2)CC3CC2CC1C3 SBXXSLRWSLQYLF-UHFFFAOYSA-N 0.000 claims 1
- GOIMYAYQMCRGNZ-UHFFFAOYSA-N 1-(2-adamantyl)-4-cyclopropyl-3-(cyclopropylmethyl)imidazol-2-one Chemical compound C1CC1C1=CN(C2C3CC4CC(C3)CC2C4)C(=O)N1CC1CC1 GOIMYAYQMCRGNZ-UHFFFAOYSA-N 0.000 claims 1
- IWDZZINNKNJGND-UHFFFAOYSA-N 1-(2-adamantyl)-4-cyclopropyl-3-methylimidazol-2-one Chemical compound C=1N(C2C3CC4CC(C3)CC2C4)C(=O)N(C)C=1C1CC1 IWDZZINNKNJGND-UHFFFAOYSA-N 0.000 claims 1
- FMESUKRQANBIAY-UHFFFAOYSA-N 1-(2-adamantyl)-4-phenyl-3-propan-2-ylimidazol-2-one Chemical compound C=1N(C2C3CC4CC(C3)CC2C4)C(=O)N(C(C)C)C=1C1=CC=CC=C1 FMESUKRQANBIAY-UHFFFAOYSA-N 0.000 claims 1
- YBKOKWBGXBVVOS-UHFFFAOYSA-N 1-(2-adamantyl)-4-propan-2-yl-3-(pyridin-2-ylmethyl)imidazol-2-one Chemical compound CC(C)C1=CN(C2C3CC4CC(C3)CC2C4)C(=O)N1CC1=CC=CC=N1 YBKOKWBGXBVVOS-UHFFFAOYSA-N 0.000 claims 1
- GDOBAHJVBZQCFD-UHFFFAOYSA-N 1-(2-adamantyl)-4-propan-2-ylimidazolidin-2-one Chemical compound O=C1NC(C(C)C)CN1C1C(C2)CC3CC2CC1C3 GDOBAHJVBZQCFD-UHFFFAOYSA-N 0.000 claims 1
- ALSATGAPVCFGPZ-UHFFFAOYSA-N 1-cyclopropyl-3-(2,4-dimethoxyphenyl)-1,3-diazaspiro[4.5]decan-2-one Chemical compound COC1=CC(OC)=CC=C1N1C(=O)N(C2CC2)C2(CCCCC2)C1 ALSATGAPVCFGPZ-UHFFFAOYSA-N 0.000 claims 1
- HZRNJHXFYZCCME-UHFFFAOYSA-N 1-cyclopropyl-3-(4-methoxyphenyl)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)N(C2CC2)C2(CCC(CC2)C=2C=CC=CC=2)C1 HZRNJHXFYZCCME-UHFFFAOYSA-N 0.000 claims 1
- RNHNFMKGDYMCTQ-UHFFFAOYSA-N 1-cyclopropyl-3-[4-methoxy-2-(trifluoromethyl)phenyl]-1,3-diazaspiro[4.6]undecan-2-one Chemical compound FC(F)(F)C1=CC(OC)=CC=C1N1C(=O)N(C2CC2)C2(CCCCCC2)C1 RNHNFMKGDYMCTQ-UHFFFAOYSA-N 0.000 claims 1
- 102100036506 11-beta-hydroxysteroid dehydrogenase 1 Human genes 0.000 claims 1
- 101710186107 11-beta-hydroxysteroid dehydrogenase 1 Proteins 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- MJLLKCYGALUGGZ-UHFFFAOYSA-N 3-(1-adamantyl)-5-(2-methylpropyl)-1h-imidazol-2-one Chemical compound O=C1NC(CC(C)C)=CN1C1(C2)CC(C3)CC2CC3C1 MJLLKCYGALUGGZ-UHFFFAOYSA-N 0.000 claims 1
- VOFZVVJSOANSPM-UHFFFAOYSA-N 3-(1-adamantyl)-5-propan-2-yl-1h-imidazol-2-one Chemical compound O=C1NC(C(C)C)=CN1C1(C2)CC(C3)CC2CC3C1 VOFZVVJSOANSPM-UHFFFAOYSA-N 0.000 claims 1
- QYRSIQXJRNOEQT-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-5-(2-methylpropyl)-1h-imidazol-2-one Chemical compound O=C1NC(CC(C)C)=CN1C1=CC=C(F)C=C1F QYRSIQXJRNOEQT-UHFFFAOYSA-N 0.000 claims 1
- UCYVWOQNWYUFPO-UHFFFAOYSA-N 3-(2-adamantyl)-5-(2,2,2-trifluoroethyl)-1h-imidazol-2-one Chemical compound O=C1NC(CC(F)(F)F)=CN1C1C(C2)CC3CC2CC1C3 UCYVWOQNWYUFPO-UHFFFAOYSA-N 0.000 claims 1
- ZBQDWGWZIOZWND-UHFFFAOYSA-N 3-(2-adamantyl)-5-(2,2-dimethylpropyl)-1h-imidazol-2-one Chemical compound O=C1NC(CC(C)(C)C)=CN1C1C(C2)CC3CC2CC1C3 ZBQDWGWZIOZWND-UHFFFAOYSA-N 0.000 claims 1
- MCEMGUQNQNZQHD-UHFFFAOYSA-N 3-(2-adamantyl)-5-(2-methylpropyl)-1h-imidazol-2-one Chemical compound O=C1NC(CC(C)C)=CN1C1C(C2)CC3CC2CC1C3 MCEMGUQNQNZQHD-UHFFFAOYSA-N 0.000 claims 1
- KAEYQFXKYXHBRH-UHFFFAOYSA-N 3-(2-adamantyl)-5-(cyclopropylmethyl)-1h-imidazol-2-one Chemical compound C=1N(C2C3CC4CC(C3)CC2C4)C(=O)NC=1CC1CC1 KAEYQFXKYXHBRH-UHFFFAOYSA-N 0.000 claims 1
- GIBQQYPWHBEYDJ-UHFFFAOYSA-N 3-(2-adamantyl)-5-[(3-fluorophenyl)methyl]-1h-imidazol-2-one Chemical compound FC1=CC=CC(CC=2NC(=O)N(C3C4CC5CC(C4)CC3C5)C=2)=C1 GIBQQYPWHBEYDJ-UHFFFAOYSA-N 0.000 claims 1
- XZFPXURTRUFBSQ-UHFFFAOYSA-N 3-(2-adamantyl)-5-benzyl-4-propan-2-yl-1h-imidazol-2-one Chemical compound N1C(=O)N(C2C3CC4CC(C3)CC2C4)C(C(C)C)=C1CC1=CC=CC=C1 XZFPXURTRUFBSQ-UHFFFAOYSA-N 0.000 claims 1
- JGMOKSVCFLDPAV-UHFFFAOYSA-N 3-(2-adamantyl)-5-cyclohexyl-1h-imidazol-2-one Chemical compound C=1N(C2C3CC4CC(C3)CC2C4)C(=O)NC=1C1CCCCC1 JGMOKSVCFLDPAV-UHFFFAOYSA-N 0.000 claims 1
- CXNMSSCUBVWWTC-UHFFFAOYSA-N 3-(2-adamantyl)-5-cyclopropyl-1h-imidazol-2-one Chemical compound C=1N(C2C3CC4CC(C3)CC2C4)C(=O)NC=1C1CC1 CXNMSSCUBVWWTC-UHFFFAOYSA-N 0.000 claims 1
- NHNVGGIKAUQSNX-UHFFFAOYSA-N 3-(2-adamantyl)-5-phenyl-1h-imidazol-2-one Chemical compound C=1N(C2C3CC4CC(C3)CC2C4)C(=O)NC=1C1=CC=CC=C1 NHNVGGIKAUQSNX-UHFFFAOYSA-N 0.000 claims 1
- AJPFEBWPOUXJPI-UHFFFAOYSA-N 3-(2-adamantyl)-5-propan-2-yl-1h-imidazol-2-one Chemical compound O=C1NC(C(C)C)=CN1C1C(C2)CC3CC2CC1C3 AJPFEBWPOUXJPI-UHFFFAOYSA-N 0.000 claims 1
- GBMJFPDFDWAPNW-UHFFFAOYSA-N 3-(2-adamantyl)-5-tert-butyl-1h-imidazol-2-one Chemical compound O=C1NC(C(C)(C)C)=CN1C1C(C2)CC3CC2CC1C3 GBMJFPDFDWAPNW-UHFFFAOYSA-N 0.000 claims 1
- HIQIJXPLXHECOQ-UHFFFAOYSA-N 3-(2-methoxyphenyl)-5-(2-methylpropyl)-1h-imidazol-2-one Chemical compound COC1=CC=CC=C1N1C(=O)NC(CC(C)C)=C1 HIQIJXPLXHECOQ-UHFFFAOYSA-N 0.000 claims 1
- ZZRNQLISGIIRNV-UHFFFAOYSA-N 3-(3-chloro-4-hydroxyphenyl)-1-cyclopropyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound C1=C(Cl)C(O)=CC=C1N1C(=O)N(C2CC2)C2(CCCCC2)C1 ZZRNQLISGIIRNV-UHFFFAOYSA-N 0.000 claims 1
- QBEBGSSUNGHEQY-UHFFFAOYSA-N 3-(3-chloro-4-methoxyphenyl)-1-cyclopropyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1N1C(=O)N(C2CC2)C2(CCCCC2)C1 QBEBGSSUNGHEQY-UHFFFAOYSA-N 0.000 claims 1
- CHRNZUIZRJYJSL-UHFFFAOYSA-N 3-(5,7-dihydroxy-2-adamantyl)-1,3-diazaspiro[4.4]nonan-2-one Chemical compound C1C(O)(C2)CC3CC2(O)CC1C3N(C(N1)=O)CC21CCCC2 CHRNZUIZRJYJSL-UHFFFAOYSA-N 0.000 claims 1
- NGHAEHALBJATBB-UHFFFAOYSA-N 3-(cyclobutylmethyl)-4-(2-methylpropyl)-1-[2-(trifluoromethyl)phenyl]imidazol-2-one Chemical compound O=C1N(CC2CCC2)C(CC(C)C)=CN1C1=CC=CC=C1C(F)(F)F NGHAEHALBJATBB-UHFFFAOYSA-N 0.000 claims 1
- BGSIVHBHUQAKCR-UHFFFAOYSA-N 3-(cyclopropylmethyl)-1-(2-methoxyphenyl)-4-(2-methylpropyl)imidazol-2-one Chemical compound COC1=CC=CC=C1N1C(=O)N(CC2CC2)C(CC(C)C)=C1 BGSIVHBHUQAKCR-UHFFFAOYSA-N 0.000 claims 1
- LAQQBOKOMUGBAV-UHFFFAOYSA-N 3-(cyclopropylmethyl)-4-(2-methylpropyl)-1-[2-(trifluoromethoxy)phenyl]imidazol-2-one Chemical compound O=C1N(CC2CC2)C(CC(C)C)=CN1C1=CC=CC=C1OC(F)(F)F LAQQBOKOMUGBAV-UHFFFAOYSA-N 0.000 claims 1
- XRPNELSAXNRATK-UHFFFAOYSA-N 3-(cyclopropylmethyl)-4-(2-methylpropyl)-1-[2-(trifluoromethyl)phenyl]imidazol-2-one Chemical compound O=C1N(CC2CC2)C(CC(C)C)=CN1C1=CC=CC=C1C(F)(F)F XRPNELSAXNRATK-UHFFFAOYSA-N 0.000 claims 1
- VOMBBEVQLBOHOP-UHFFFAOYSA-N 3-(cyclopropylmethyl)-4-propan-2-yl-1-[2-(trifluoromethyl)phenyl]imidazol-2-one Chemical compound O=C1N(CC2CC2)C(C(C)C)=CN1C1=CC=CC=C1C(F)(F)F VOMBBEVQLBOHOP-UHFFFAOYSA-N 0.000 claims 1
- NEPPBZNFPJEDSG-UHFFFAOYSA-N 3-[1-(4-chlorophenyl)cyclopropyl]-5-propan-2-yl-1h-imidazol-2-one Chemical compound O=C1NC(C(C)C)=CN1C1(C=2C=CC(Cl)=CC=2)CC1 NEPPBZNFPJEDSG-UHFFFAOYSA-N 0.000 claims 1
- PFPAVXKLHRSKFP-UHFFFAOYSA-N 3-benzyl-1-(2,5-dichlorophenyl)-4-propan-2-ylimidazolidin-2-one Chemical compound CC(C)C1CN(C=2C(=CC=C(Cl)C=2)Cl)C(=O)N1CC1=CC=CC=C1 PFPAVXKLHRSKFP-UHFFFAOYSA-N 0.000 claims 1
- GPEXTVMRDYFDDR-UHFFFAOYSA-N 3-benzyl-1-(2-chloro-5-fluorophenyl)-4-propan-2-ylimidazolidin-2-one Chemical compound CC(C)C1CN(C=2C(=CC=C(F)C=2)Cl)C(=O)N1CC1=CC=CC=C1 GPEXTVMRDYFDDR-UHFFFAOYSA-N 0.000 claims 1
- BMBJKNCWPIXDEY-UHFFFAOYSA-N 3-chloro-4-(2'-oxospiro[1,3-dihydroindene-2,4'-imidazolidine]-1'-yl)benzonitrile Chemical compound ClC1=CC(C#N)=CC=C1N1C(=O)NC2(CC3=CC=CC=C3C2)C1 BMBJKNCWPIXDEY-UHFFFAOYSA-N 0.000 claims 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- JUKYJDJDPQKHPB-UHFFFAOYSA-N 3-cyclopropyl-1-(3-fluoro-4-methoxyphenyl)-4-propan-2-ylimidazolidin-2-one Chemical compound C1=C(F)C(OC)=CC=C1N1C(=O)N(C2CC2)C(C(C)C)C1 JUKYJDJDPQKHPB-UHFFFAOYSA-N 0.000 claims 1
- CXUDMJSAOSPVMO-UHFFFAOYSA-N 3-cyclopropyl-1-(4-hydroxyphenyl)-4-propan-2-ylimidazolidin-2-one Chemical compound CC(C)C1CN(C=2C=CC(O)=CC=2)C(=O)N1C1CC1 CXUDMJSAOSPVMO-UHFFFAOYSA-N 0.000 claims 1
- GLQNRFRYMWATKC-UHFFFAOYSA-N 3-cyclopropyl-1-(4-methoxyphenyl)-4-propan-2-ylimidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)N(C2CC2)C(C(C)C)C1 GLQNRFRYMWATKC-UHFFFAOYSA-N 0.000 claims 1
- OKWQTMHZUPIAGU-UHFFFAOYSA-N 3-cyclopropyl-1-[[5-fluoro-2-(trifluoromethyl)phenyl]methyl]-4-methylimidazol-2-one Chemical compound O=C1N(C2CC2)C(C)=CN1CC1=CC(F)=CC=C1C(F)(F)F OKWQTMHZUPIAGU-UHFFFAOYSA-N 0.000 claims 1
- PGSPWNOPMZCYMC-UHFFFAOYSA-N 3-cyclopropyl-4-methyl-1-[[2-(trifluoromethyl)phenyl]methyl]imidazol-2-one Chemical compound O=C1N(C2CC2)C(C)=CN1CC1=CC=CC=C1C(F)(F)F PGSPWNOPMZCYMC-UHFFFAOYSA-N 0.000 claims 1
- JXVLWASIUUTYOK-UHFFFAOYSA-N 3-cyclopropyl-4-propan-2-yl-1-[2-(trifluoromethyl)phenyl]imidazol-2-one Chemical compound O=C1N(C2CC2)C(C(C)C)=CN1C1=CC=CC=C1C(F)(F)F JXVLWASIUUTYOK-UHFFFAOYSA-N 0.000 claims 1
- GSNQGPRWTABVHY-UHFFFAOYSA-N 3-methyl-4-(2-methylpropyl)-1-[2-(trifluoromethyl)phenyl]imidazol-2-one Chemical compound O=C1N(C)C(CC(C)C)=CN1C1=CC=CC=C1C(F)(F)F GSNQGPRWTABVHY-UHFFFAOYSA-N 0.000 claims 1
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 claims 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 1
- ZLICTKWIMNERLH-UHFFFAOYSA-N 4-(2-methylpropyl)-1-[2-(trifluoromethyl)phenyl]imidazolidin-2-one Chemical compound O=C1NC(CC(C)C)CN1C1=CC=CC=C1C(F)(F)F ZLICTKWIMNERLH-UHFFFAOYSA-N 0.000 claims 1
- JPSYDOWOUADWOE-UHFFFAOYSA-N 4-benzyl-3-cyclopropyl-1-(2,5-dichlorophenyl)imidazolidin-2-one Chemical compound ClC1=CC=C(Cl)C(N2C(N(C3CC3)C(CC=3C=CC=CC=3)C2)=O)=C1 JPSYDOWOUADWOE-UHFFFAOYSA-N 0.000 claims 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims 1
- UJZYYYDCEDIHOQ-UHFFFAOYSA-N 5-(2-methylpropyl)-3-[2-(trifluoromethoxy)phenyl]-1h-imidazol-2-one Chemical compound O=C1NC(CC(C)C)=CN1C1=CC=CC=C1OC(F)(F)F UJZYYYDCEDIHOQ-UHFFFAOYSA-N 0.000 claims 1
- ZCZDSQBCYDZREN-UHFFFAOYSA-N 5-(2-methylpropyl)-3-[2-(trifluoromethyl)phenyl]-1h-imidazol-2-one Chemical compound O=C1NC(CC(C)C)=CN1C1=CC=CC=C1C(F)(F)F ZCZDSQBCYDZREN-UHFFFAOYSA-N 0.000 claims 1
- IXENFYCEYYEYIG-UHFFFAOYSA-N 5-(2-methylpropyl)-3-[2-methyl-6-(trifluoromethyl)phenyl]-1h-imidazol-2-one Chemical compound O=C1NC(CC(C)C)=CN1C1=C(C)C=CC=C1C(F)(F)F IXENFYCEYYEYIG-UHFFFAOYSA-N 0.000 claims 1
- YNIYLGQXULJDND-UHFFFAOYSA-N 5-(2-methylpropyl)-4-(2,2,2-trifluoroethyl)-3-[2-(trifluoromethyl)phenyl]-1h-imidazol-2-one Chemical compound FC(F)(F)CC1=C(CC(C)C)NC(=O)N1C1=CC=CC=C1C(F)(F)F YNIYLGQXULJDND-UHFFFAOYSA-N 0.000 claims 1
- NVDMAUQJEKWPJT-UHFFFAOYSA-N 5-propan-2-yl-3-[2-(trifluoromethyl)phenyl]-1h-imidazol-2-one Chemical compound O=C1NC(C(C)C)=CN1C1=CC=CC=C1C(F)(F)F NVDMAUQJEKWPJT-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- GJMWPFWEEHDAPH-UHFFFAOYSA-N CC(CCCCC)N1C(NC(=C1)C(C)(C)C)=O Chemical compound CC(CCCCC)N1C(NC(=C1)C(C)(C)C)=O GJMWPFWEEHDAPH-UHFFFAOYSA-N 0.000 claims 1
- DZBUPNPEJPOEBS-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1=C(C=CC(=C1)O)N1C(N(C2(C1)CCCCC2)C1CC1)=O Chemical compound ClC=1C=C(C=CC=1)C1=C(C=CC(=C1)O)N1C(N(C2(C1)CCCCC2)C1CC1)=O DZBUPNPEJPOEBS-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- HSSBCWGXEURJEY-UHFFFAOYSA-N spiro[2h-naphthalene-1,4'-imidazolidine]-2'-one Chemical compound N1C(=O)NCC11C2=CC=CC=C2C=CC1 HSSBCWGXEURJEY-UHFFFAOYSA-N 0.000 claims 1
- NHZYPQKIIIJXGY-UHFFFAOYSA-N spiro[imidazolidine-4,2'-indene]-2-one Chemical compound O=C1NCC2(N1)C=c1ccccc1=C2 NHZYPQKIIIJXGY-UHFFFAOYSA-N 0.000 claims 1
- 0 *C(*)(C1N2*)C(*)(*)[C@@]1N(*)C2=O Chemical compound *C(*)(C1N2*)C(*)(*)[C@@]1N(*)C2=O 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/10—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Nutrition Science (AREA)
- Child & Adolescent Psychology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1. Соединения формулы ! ! в которой R1 означает ! а) адамантил, гидроксиадамантил или трифтометилфенил; ! R2 означает водород, метил, этил или циклопропил; ! один из R3 и R4 означает водород, алкил, циклоалкил, галоалкил или отсутствует, а другой означает ! a) водород, алкил, пиридинил, циклоалкил, циклоалкилалкил или галоалкил; ! b) фенил или фенил, замещенный одним-тремя заместителями, независимо выбранными из фтора, хлора, брома, галоалкила, алкокси, гидрокси и галоалкокси; ! c) фенилалкил или пиридинилалкил, где фенилалкил и пиридинилалкил необязательно замещены одним-тремя заместителями, независимо выбранными из алкила, галоида, галоалкила и гидрокси; ! d) оксетан или оксетан, замещенный алкилом; ! e) нафтил или тетрагидронафтил; ! f) фенилалкоксиалкил или фенилалкоксиалкил, замещенный одним-тремя заместителями, независимо выбранными из алкила и галоида; ! g) гидроксиалкил; ! h) пиридинилоксиалкил или пиридинилоксиалкил, замещенный цианогруппой; ! или R3 и R4 вместе с атомом углерода, к которому они присоединены, образуют циклоалкан, пиперидин, тетрагидропиран, тетрагидротиопиран, пирролидин, тетрагидрофуран, индан или оксетан, где циклоалкил, пиперидин, тетрагидропиран, тетрагидротиопиран, пирролидин, тетрагидрофуран, индан и оксетан необязательно замещены одним-тремя заместителями, независимо выбранными из алкила, арила и арилалкила; ! один из R5 и R6 означает водород, изопропил, изобутил, циклоалкил или галоалкил, а другой означает водород или отсутствует; !и их фармацевтически приемлемые соли и эфиры при условии, что исключается 1,3-дигидро-4-фенил-1-(3-(трифторметил)фенил)-2Н-имидазол-2-он и что в случае, если один из R3 и R4 оз 1. The compounds of the formula! ! in which R1 means! a) adamantyl, hydroxyadamantyl or triftomethylphenyl; ! R2 is hydrogen, methyl, ethyl or cyclopropyl; ! one of R3 and R4 means hydrogen, alkyl, cycloalkyl, haloalkyl or absent, and the other means! a) hydrogen, alkyl, pyridinyl, cycloalkyl, cycloalkylalkyl or haloalkyl; ! b) phenyl or phenyl substituted with one to three substituents independently selected from fluoro, chloro, bromo, haloalkyl, alkoxy, hydroxy and haloalkoxy; ! c) phenylalkyl or pyridinylalkyl, where phenylalkyl and pyridinylalkyl are optionally substituted with one to three substituents independently selected from alkyl, halogen, haloalkyl and hydroxy; ! d) oxetane or oxetane substituted with alkyl; ! e) naphthyl or tetrahydronaphthyl; ! f) phenylalkoxyalkyl or phenylalkoxyalkyl substituted with one to three substituents independently selected from alkyl and halogen; ! g) hydroxyalkyl; ! h) pyridinyloxyalkyl or pyridinyloxyalkyl substituted with cyano; ! or R3 and R4, together with the carbon atom to which they are attached, form cycloalkane, piperidine, tetrahydropyran, tetrahydrothiopyran, pyrrolidine, tetrahydrofuran, indane or oxetane, where cycloalkyl, piperidine, tetrahydropyran, tetrahydrothiopyran, pyrrolidine, optionally, - three substituents independently selected from alkyl, aryl and arylalkyl; ! one of R5 and R6 means hydrogen, isopropyl, isobutyl, cycloalkyl or haloalkyl, and the other means hydrogen or is absent; ! and their pharmaceutically acceptable salts and esters, provided that 1,3-dihydro-4-phenyl-1- (3- (trifluoromethyl) phenyl) -2H-imidazol-2-one is excluded and that if one of R3 and r4 oz
Claims (21)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06122591.8 | 2006-10-19 | ||
| EP06122591 | 2006-10-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009118488A true RU2009118488A (en) | 2010-11-27 |
| RU2439062C2 RU2439062C2 (en) | 2012-01-10 |
Family
ID=39259578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009118488/04A RU2439062C2 (en) | 2006-10-19 | 2007-10-09 | Imidazolone and imidazolidinone derivatives as 11b-hsd1 inhibitors for diabetes |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8129423B2 (en) |
| EP (2) | EP2308851A1 (en) |
| JP (1) | JP5079011B2 (en) |
| KR (2) | KR20110079776A (en) |
| CN (1) | CN101553474B (en) |
| AR (1) | AR063332A1 (en) |
| AU (1) | AU2007312391B2 (en) |
| BR (1) | BRPI0717657A2 (en) |
| CA (1) | CA2666489C (en) |
| CL (1) | CL2007002972A1 (en) |
| IL (1) | IL197955A0 (en) |
| MX (1) | MX2009003939A (en) |
| NO (1) | NO20091548L (en) |
| PE (1) | PE20080890A1 (en) |
| RU (1) | RU2439062C2 (en) |
| TW (1) | TWI339120B (en) |
| WO (1) | WO2008046758A2 (en) |
| ZA (1) | ZA200902638B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8278318B2 (en) | 2007-06-21 | 2012-10-02 | Incyte Corporation | Spirocycles as inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1 |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2666762C (en) | 2006-10-19 | 2014-12-30 | F. Hoffmann-La Roche Ag | Aminomethyl-4-imidazoles |
| BRPI0717657A2 (en) | 2006-10-19 | 2013-12-24 | Hoffmann La Roche | COMPOUNDS, PROCESS FOR THE PREPARATION OF A COMPOUND, PHARMACEUTICAL COMPOSITION UNDERSTANDING, USES OF COMPOUNDS, METHODS FOR DIABETES TREATMENT AND PROPHYLAXY, OBESITY, DIETARY DISORDER AND DIPHYPETHYDIA DYPYTHESIA |
| WO2008106128A2 (en) | 2007-02-26 | 2008-09-04 | Vitae Pharmaceuticals, Inc. | CYCLIC UREA AND CARBAMATE INHIBITORS OF 11β -HYDROXYSTEROID DEHYDROGENASE 1 |
| EP2025674A1 (en) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituted tetra hydro naphthalines, method for their manufacture and their use as drugs |
| WO2009034062A1 (en) * | 2007-09-11 | 2009-03-19 | Glaxo Group Limited | Compounds which inhibit the glycine transporter and uses thereof in medicine |
| US8440658B2 (en) | 2007-12-11 | 2013-05-14 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| US8124636B2 (en) * | 2008-04-30 | 2012-02-28 | Hoffmann-La Roche Inc. | Imidazolidinone derivatives as 11B-HSD1 inhibitors |
| WO2009134387A1 (en) * | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| CA2723032A1 (en) * | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| MX2010011935A (en) | 2008-05-01 | 2011-05-19 | Vitae Pharmaceuticals Inc | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1. |
| WO2009134392A1 (en) * | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| KR20110031355A (en) * | 2008-06-25 | 2011-03-25 | 엔비보 파마슈티칼즈, 인코퍼레이티드 | 1,2-disubstituted heterocyclic compounds |
| WO2010010150A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Synthesis of inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| EP2324017B1 (en) | 2008-07-25 | 2014-12-31 | Boehringer Ingelheim International GmbH | INHIBITORS OF 11beta-HYDROXYSTEROID DEHYDROGENASE 1 |
| NZ590495A (en) * | 2008-07-25 | 2012-10-26 | Vitae Pharmaceuticals Inc | Dihydropyridin-phenyl-3-oxazinan-2-ones as inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| JP5679997B2 (en) | 2009-02-04 | 2015-03-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Cyclic inhibitor of 11β-hydroxysteroid dehydrogenase 1 |
| UA109255C2 (en) | 2009-04-30 | 2015-08-10 | Берінгер Інгельхайм Інтернешнл Гмбх | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2440537A1 (en) * | 2009-06-11 | 2012-04-18 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure |
| US8883778B2 (en) | 2009-07-01 | 2014-11-11 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11 beta-hydroxysteroid dehydrogenase 1 |
| WO2011056737A1 (en) | 2009-11-05 | 2011-05-12 | Boehringer Ingelheim International Gmbh | Novel chiral phosphorus ligands |
| TWI531571B (en) | 2009-11-06 | 2016-05-01 | 維它藥物公司 | Aryl- and heteroarylcarbonyl derivatives of hexahydroindolopyridine and octahydrobenzoquinoline |
| WO2011107494A1 (en) | 2010-03-03 | 2011-09-09 | Sanofi | Novel aromatic glycoside derivatives, medicaments containing said compounds, and the use thereof |
| US8648192B2 (en) | 2010-05-26 | 2014-02-11 | Boehringer Ingelheim International Gmbh | 2-oxo-1,2-dihydropyridin-4-ylboronic acid derivatives |
| WO2011159760A1 (en) | 2010-06-16 | 2011-12-22 | Vitae Pharmaceuticals, Inc. | Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| EP2585444B1 (en) | 2010-06-25 | 2014-10-22 | Boehringer Ingelheim International GmbH | Azaspirohexanones as inhibitors of 11-beta-hsd1 for the treatment of metabolic disorders |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| EA201300522A1 (en) | 2010-11-02 | 2013-11-29 | Бёрингер Ингельхайм Интернациональ Гмбх | PHARMACEUTICAL COMBINATIONS FOR THE TREATMENT OF METABOLIC DISORDERS |
| TWI537258B (en) | 2010-11-05 | 2016-06-11 | 百靈佳殷格翰國際股份有限公司 | Aryl-and heteroarylcarbonyl derivatives of hexahydroindenopyridine and octahydrobenzoquinoline |
| CN102241678B (en) | 2011-04-26 | 2014-10-29 | 辽宁利锋科技开发有限公司 | Anti-tumor effect and application of compounds containing alicyclic structure |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US9340549B2 (en) | 2012-03-05 | 2016-05-17 | Amgen Inc. | Oxazolidinone compounds and derivatives thereof |
| JP2015157764A (en) * | 2012-06-14 | 2015-09-03 | 大正製薬株式会社 | Substance for inhibition of glycine transporter |
| US9126998B2 (en) | 2012-11-05 | 2015-09-08 | Bayer Pharma AG | Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| US9624214B2 (en) | 2012-11-05 | 2017-04-18 | Bayer Pharma Aktiengesellschaft | Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| US8778964B2 (en) | 2012-11-05 | 2014-07-15 | Bayer Pharma Aktiengesellschaft | Hydroxy-substituted imidazo[1,2-a]-pyridinecarboxamides and their use |
| US8796305B2 (en) | 2012-11-05 | 2014-08-05 | Bayer Pharma Aktiengesellschaft | Carboxy-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| ES2625744T3 (en) | 2013-06-04 | 2017-07-20 | Bayer Pharma Aktiengesellschaft | Imidazo [1,2-a] pyridines substituted with 3-aryl and their use |
| UY35693A (en) | 2013-08-08 | 2015-02-27 | Bayer Pharma AG | PIRAZOLO [1,5-A] PIRIDIN-3-SUBSTITUTED CARBOXAMIDS AND THEIR USE |
| JP2017507140A (en) | 2014-02-19 | 2017-03-16 | バイエル・ファルマ・アクティエンゲゼルシャフト | 3- (Pyrimidin-2-yl) imidazo [1,2-a] pyridine |
| EP3119777A1 (en) | 2014-03-21 | 2017-01-25 | Bayer Pharma Aktiengesellschaft | Cyano-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| GB201416346D0 (en) * | 2014-09-16 | 2014-10-29 | Shire Internat Gmbh | Spirocyclic derivatives |
| CN107001361A (en) | 2014-12-02 | 2017-08-01 | 拜耳医药股份有限公司 | Imidazo [1,2 a] pyridine of heteroaryl substitution and application thereof |
| US10174021B2 (en) | 2014-12-02 | 2019-01-08 | Bayer Pharma Aktiengesellschaft | Substituted pyrazolo[1,5-A]pyridines and their use |
| EP3286185A1 (en) | 2015-02-05 | 2018-02-28 | Bayer Pharma Aktiengesellschaft | Substituted pyrazolo[1,5-a]-pyridine-3-carboxamides and use thereof |
| ES2807549T3 (en) | 2016-01-13 | 2021-02-23 | Gruenenthal Gmbh | 3 - ((hetero) -aryl) -8-amino-2-oxo-1,3-diaza-spiro- [4.5] -decane derivatives |
| HRP20200809T1 (en) | 2016-01-13 | 2020-08-07 | Grünenthal GmbH | 3-(carboxymethyl)-8-amino-2-oxo-1,3-diaza-spiro-[4.5]-decane derivatives |
| MX379359B (en) | 2016-01-13 | 2025-03-11 | Gruenenthal Gmbh | DERIVATIVES OF 8-AMINO-2-OXO-1,3-DIAZA-SPIRO-[4.5]-DECane. |
| PE20181375A1 (en) | 2016-01-13 | 2018-08-28 | Gruenenthal Chemie | DERIVATIVES OF 3 - ((HETERO) ARYL) -ALKYL-8-AMINO-2-OXO-1,3-DIAZA-SPIRO- [4.5] -DECANE |
| JP6862457B2 (en) | 2016-01-13 | 2021-04-21 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 3- (Carboxymethyl) -8-amino-2-oxo-1,3-diaza-spiro- [4.5] -decane derivative |
| EP3235813A1 (en) | 2016-04-19 | 2017-10-25 | Cidqo 2012, S.L. | Aza-tetra-cyclo derivatives |
| RU2746423C2 (en) * | 2019-09-02 | 2021-04-13 | Общество с ограниченной ответственностью "Научно-исследовательский институт ХимРар" (ООО "НИИ ХимРар") | Hepatitis b virus (hbv) inhibitor |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL24005A (en) * | 1964-12-31 | 1970-05-21 | Robins Co Inc A H | 1,3-disubstituted-4-(2-substituted-ethyl)-2-imidazolidinones,processes for their production and pharmaceutical compositions containing them |
| GB1173492A (en) | 1966-02-18 | 1969-12-10 | Upjohn Co | Acylamino-Adamantane Derivatives |
| US3625956A (en) | 1967-12-08 | 1971-12-07 | Ciba Geigy Corp | 1-phenyl-4-alkyl-2-imidazolone derivatives |
| CH547288A (en) * | 1971-06-23 | 1974-03-29 | Ciba Geigy Ag | PROCESS FOR MANUFACTURING NEW HETEROCYCLIC SUBSTANCES. |
| GB9000725D0 (en) | 1990-01-12 | 1990-03-14 | Pfizer Ltd | Therapeutic agents |
| US5164403A (en) | 1991-04-05 | 1992-11-17 | G. D. Searle & Co. | N-arylheteroarylalkyl imidazol-2-one compounds for treatment of circulatory disorders |
| US5861420A (en) * | 1991-04-05 | 1999-01-19 | G. D. Searle & Co. | N-arylheteroarylalkyl imidazol-2-one compounds for treatment of circulatory disorders |
| TW218017B (en) * | 1992-04-28 | 1993-12-21 | Takeda Pharm Industry Co Ltd | |
| RU2238937C2 (en) * | 1998-12-24 | 2004-10-27 | Фудзисава Фармасьютикал Ко., Лтд. | Derivatives of imidazole, pharmaceutical composition and method for prophylaxis and/or treatment based on thereof |
| AU2001288605A1 (en) * | 2000-09-06 | 2002-03-22 | Chugai Seiyaku Kabushiki Kaisha | A traceless solid-phase synthesis of 2-imidazolones |
| EP1542667B1 (en) * | 2002-07-24 | 2012-03-07 | PTC Therapeutics, Inc. | Ureido substituted benzoic acid compounds and their use for nonsense suppression and the treatment of disease |
| EA011021B1 (en) * | 2004-05-07 | 2008-12-30 | Янссен Фармацевтика Н.В. | Adamantyl pyrrolidin -2-one derivatives as 11 beta hydroxysteroid dehydrogenase inhibitors |
| AU2005279209B2 (en) * | 2004-08-30 | 2011-03-24 | Janssen Pharmaceutica N.V. | Tricyclic lactam derivatives as 11-BETA hydroxysteroid dehydrogenase inhibitors |
| AU2006204017B2 (en) * | 2005-01-05 | 2011-10-06 | Abbvie Inc. | Adamantyl derivatives as inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme |
| EP1864971A4 (en) * | 2005-03-31 | 2010-02-10 | Takeda Pharmaceutical | PROPHYLACTIC / THERAPEUTIC AGENT FOR DIABETES |
| JP4870778B2 (en) * | 2005-12-01 | 2012-02-08 | エフ.ホフマン−ラ ロシュ アーゲー | 2,4,5-Triphenylimidazoline derivatives as inhibitors of the interaction between P53 and MDM2 proteins used as anticancer agents |
| UY30097A1 (en) | 2006-01-20 | 2007-08-31 | Atugen Ag | THERAPEUTIC USES OF RTP801 INHIBITORS |
| JP2007254409A (en) * | 2006-03-24 | 2007-10-04 | Taisho Pharmaceut Co Ltd | Imidazolidinone derivatives |
| WO2008044656A1 (en) * | 2006-10-06 | 2008-04-17 | Taisho Pharmaceutical Co., Ltd. | Imidazolidinone derivative |
| BRPI0717657A2 (en) | 2006-10-19 | 2013-12-24 | Hoffmann La Roche | COMPOUNDS, PROCESS FOR THE PREPARATION OF A COMPOUND, PHARMACEUTICAL COMPOSITION UNDERSTANDING, USES OF COMPOUNDS, METHODS FOR DIABETES TREATMENT AND PROPHYLAXY, OBESITY, DIETARY DISORDER AND DIPHYPETHYDIA DYPYTHESIA |
| CL2007002994A1 (en) | 2006-10-19 | 2008-02-08 | Wyeth Corp | HETEROCICLIC DERIVATIVE COMPOUNDS CONTAINING SULFAMOIL, INHIBITORS OF HSP90; PHARMACEUTICAL COMPOSITION; AND USE FOR THE TREATMENT OF CANCER, SUCH AS CANCER OF BREAST, COLON AND PROSTATE, BETWEEN OTHERS. |
| CA2666762C (en) * | 2006-10-19 | 2014-12-30 | F. Hoffmann-La Roche Ag | Aminomethyl-4-imidazoles |
| CN101528709B (en) * | 2006-10-19 | 2012-02-01 | 弗·哈夫曼-拉罗切有限公司 | Aminomethyl-2-imidazoles with affinity with the trace amine associated receptors |
-
2007
- 2007-10-09 BR BRPI0717657-0A2A patent/BRPI0717657A2/en not_active IP Right Cessation
- 2007-10-09 KR KR1020117013229A patent/KR20110079776A/en not_active Withdrawn
- 2007-10-09 EP EP10175995A patent/EP2308851A1/en not_active Withdrawn
- 2007-10-09 WO PCT/EP2007/060667 patent/WO2008046758A2/en not_active Ceased
- 2007-10-09 CA CA2666489A patent/CA2666489C/en not_active Expired - Fee Related
- 2007-10-09 RU RU2009118488/04A patent/RU2439062C2/en not_active IP Right Cessation
- 2007-10-09 AU AU2007312391A patent/AU2007312391B2/en not_active Ceased
- 2007-10-09 JP JP2009532768A patent/JP5079011B2/en not_active Expired - Fee Related
- 2007-10-09 EP EP07821040A patent/EP2104665A2/en not_active Withdrawn
- 2007-10-09 CN CN2007800387224A patent/CN101553474B/en not_active Expired - Fee Related
- 2007-10-09 MX MX2009003939A patent/MX2009003939A/en not_active Application Discontinuation
- 2007-10-09 KR KR1020097007936A patent/KR101118410B1/en not_active Expired - Fee Related
- 2007-10-12 US US11/871,318 patent/US8129423B2/en not_active Expired - Fee Related
- 2007-10-16 TW TW096138731A patent/TWI339120B/en not_active IP Right Cessation
- 2007-10-17 PE PE2007001408A patent/PE20080890A1/en not_active Application Discontinuation
- 2007-10-17 CL CL200702972A patent/CL2007002972A1/en unknown
- 2007-10-17 AR ARP070104597A patent/AR063332A1/en not_active Application Discontinuation
-
2009
- 2009-04-05 IL IL197955A patent/IL197955A0/en unknown
- 2009-04-16 ZA ZA200902638A patent/ZA200902638B/en unknown
- 2009-04-20 NO NO20091548A patent/NO20091548L/en not_active Application Discontinuation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8278318B2 (en) | 2007-06-21 | 2012-10-02 | Incyte Corporation | Spirocycles as inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1 |
| US9006260B2 (en) | 2007-06-21 | 2015-04-14 | Incyte Corporation | Spirocycles as inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1 |
| US9371323B2 (en) | 2007-06-21 | 2016-06-21 | Incyte Holdings Corporation | Spirocycles as inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1 |
| US9873698B2 (en) | 2007-06-21 | 2018-01-23 | Incyte Holdings Corporation | Spirocycles as inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1 |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200902638B (en) | 2010-03-31 |
| CN101553474B (en) | 2013-02-27 |
| CA2666489A1 (en) | 2008-04-24 |
| AU2007312391B2 (en) | 2012-06-21 |
| PE20080890A1 (en) | 2008-06-28 |
| US20080103183A1 (en) | 2008-05-01 |
| KR101118410B1 (en) | 2012-04-23 |
| RU2439062C2 (en) | 2012-01-10 |
| AR063332A1 (en) | 2009-01-21 |
| WO2008046758A3 (en) | 2009-06-11 |
| EP2104665A2 (en) | 2009-09-30 |
| MX2009003939A (en) | 2009-05-11 |
| EP2308851A1 (en) | 2011-04-13 |
| CL2007002972A1 (en) | 2008-05-30 |
| JP5079011B2 (en) | 2012-11-21 |
| US8129423B2 (en) | 2012-03-06 |
| CN101553474A (en) | 2009-10-07 |
| WO2008046758A2 (en) | 2008-04-24 |
| KR20110079776A (en) | 2011-07-07 |
| AU2007312391A1 (en) | 2008-04-24 |
| BRPI0717657A2 (en) | 2013-12-24 |
| KR20090065535A (en) | 2009-06-22 |
| NO20091548L (en) | 2009-05-05 |
| JP2010506876A (en) | 2010-03-04 |
| CA2666489C (en) | 2012-10-02 |
| IL197955A0 (en) | 2009-12-24 |
| TW200831088A (en) | 2008-08-01 |
| TWI339120B (en) | 2011-03-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2009118488A (en) | IMIDAZOLONE AND IMIDAZOLIDINONE DERIVATIVES AS 11B-HSD1 DIABETES INHIBITORS | |
| RU2379292C2 (en) | Pyrazole derivatives as phosphodiesterase 4 inhibitors | |
| RU2320664C2 (en) | Derivatives of 1'-(2-hydroxy-3-aryloxypropyl-1-yl)-substituted spiro[benzofuran-piperidines], spiro[benzofuran-pyrrolidines] and spiro[chromen-piperidines], method for their preparing, intermediate compound and method for its preparing, pharmaceutical composition, using | |
| RU2352567C2 (en) | Terahydrochinoline derivatives demonstrating activity preotective against hiv | |
| RU2011137454A (en) | AGONISTS AND ANTAGONISTS OF S1P5-RECEPTORS AND WAYS OF THEIR APPLICATION | |
| RU2399620C2 (en) | Quinuclidine derivatives and use thereof as m3 muscarinic receptor antagonists | |
| RU2005124360A (en) | NEW REVERSE ACCEPTORS OF RECEPTOR NE 1 | |
| RU2012139828A (en) | Pyrazolopyiperidine derivatives as Nadph Oxidase Inhibitors | |
| RU2011146872A (en) | DERIVATIVES OF VALLEY AS CATATEPSIN INHIBITORS | |
| RU2010148534A (en) | IMIDAZOLIDINONE DERIVATIVES AS INHIBITORS IN 11B-HSD1 | |
| RU2008103483A (en) | Pyridazine derivatives | |
| RU2011116232A (en) | PYRAZOLOPYRIDINE DERIVATIVES AS NADPH-OXIDASE INHIBITORS | |
| JPWO2006022428A1 (en) | Diabetes treatment | |
| JP2021175759A (en) | Methods and compositions for improving cognitive function | |
| RU2015106787A (en) | SUBSTITUTED PYRROLES ACTIVE AS KINASE INHIBITORS | |
| RU2009105818A (en) | Pyrazoles as glucokinase activators | |
| RU2004115333A (en) | 4- (4-ALCOXY-3-HYDROXYPHENYL) -2-pyrrolidone derivatives as PDE-4 INHIBITORS FOR THE TREATMENT OF NEUROLOGICAL SYNDROMES | |
| RU2010128240A (en) | AMINOPYRAZOLE DERIVATIVES | |
| RU2007106180A (en) | Derivatives of indole, indazole or indoline | |
| FI3478284T3 (en) | Compounds and compositions for the treatment of cancer | |
| RU2019104609A (en) | AMINOPYRIDINE DERIVATIVES AND THEIR USE AS SELECTIVE ALK-2 INHIBITORS | |
| RU2407737C2 (en) | Pyrazolone derivatives | |
| RU2006128445A (en) | ACETYLINE PIPERAZINE COMPOUNDS AND THEIR APPLICATION AS ANTAGONISTS OF METABOTROPIC GLUTAMATE RECEPTORS | |
| RU2007107374A (en) | OXOPIPERIDINE DERIVATIVES, THEIR PRODUCTION AND APPLICATION IN THERAPY | |
| RU2007130706A (en) | SUBSTITUTED 4-Phenyltetrahydroisoquinolines, METHOD FOR PRODUCING THEM, THEIR APPLICATION AS MEDICINES, AND ALSO CONTAINING THEIR MEDICINES |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20141010 |